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The best holiday homes in Winchester

Check out our pick of great holiday homes in Winchester

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Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

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The spacious holiday home is fitted with 4 bedrooms, 2 bathrooms, bed linen, towels, a flat-screen TV with streaming services, a dining area, a fully equipped kitchen, and a terrace with garden views. For added privacy, the accommodation features a private entrance.

Very clean and tidy. Clear instructions for entry. Came back to me quickly when I had a query.

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9.2
Superb
13 reviews
Price from
€ 420
per night

This holiday home has 3 bedrooms, a kitchen with an oven and a toaster, a flat-screen TV, a seating area and 1 bathroom fitted with a bath. Towels and bed linen are offered in the holiday home. The property has an outdoor dining area.

Spacious home. Perfect location. Quiet.

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9.4
Superb
45 reviews
Price from
€ 264
per night

Situated in Winchester and only 19 km from The Mayflower Theatre, 4 Bed City House with Private Garden and Parking features accommodation with garden views, free WiFi and free private parking. The property features city and inner courtyard views, and is 20 km from Southampton Guildhall. Outdoor dining is also possible at the holiday home.

Very convenient location for town and the university (we were moving our daughter in for her second year). The house was very well-presented,equipped and spacious.

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9.5
Exceptional
28 reviews
Price from
€ 343
per night

The spacious holiday home comes with 3 bedrooms, a flat-screen TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are provided in the holiday home. The property has an outdoor dining area.

The location was fabulous. Easy to get to the centre of things.

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9.2
Superb
26 reviews
Price from
€ 250
per night

The spacious holiday home features 3 bedrooms, 3 bathrooms, bed linen, towels, a flat-screen TV with streaming services, a dining area, a fully equipped kitchen, and a patio with river views. A private entrance leads guests into the holiday home, where they can enjoy some chocolates or cookies. The property has an outdoor dining area.

Great location, lovely that the property backs up to the river. Very tastefully done, lovely house. Owners were very nice and responsive. I can highly recommend :)

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9.2
Superb
27 reviews
Price from
€ 250
per night

The spacious holiday home has 4 bedrooms, 3 bathrooms, bed linen, towels, a flat-screen TV, a dining area, a fully equipped kitchen, and a patio with garden views. For added privacy, the accommodation features a private entrance.

Amazing spacious place! Very clean and easy check in.

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9.4
Superb
37 reviews
Price from
€ 266
per night

Providing a garden, a bar and free WiFi, No2 St Peters Street is a recently renovated holiday home 20 km from The Mayflower Theatre and 20 km from Southampton Guildhall. The property features inner courtyard and quiet street views, and is 25 km from Ageas Bowl. The property is non-smoking and is located 21 km from Southampton Cruise Terminal.

Facilities were fantastic, and the host was speedy and very helpful with entering the building. TV room was a great addition and ensured we had a great time at the venue. Easy access to the rest of the city and close by to lots of restaurants etc.

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9.6
Exceptional
8 reviews
Price from
€ 432
per night

The recently renovated holiday home is equipped with 2 bedrooms, a flat-screen TV with streaming services and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. A private entrance leads guests into the holiday home, where they can enjoy some wine or champagne and chocolates or cookies. There is also a seating area and a fireplace.

I loved everything about the property! It was my first time staying in Winchester and this cozy cottage was the perfect pick for us! I rented it for my husband and our two granddaughters that live nearby. Julia, the owner and host was helpful at every turn. She was over the top accommodating! The cottage was impeccably clean and tidy and stocked full of everything a traveler would need. The beds were very comfortable with great linens. The location of the Nestle House was walking distance to the Cathedral, shopping and any food preferences you might have. We were so happy we found this spot!

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9.5
Exceptional
12 reviews
Price from
€ 257
per night

The holiday home has 2 bedrooms, a TV, a fully equipped kitchen with a dishwasher and kitchenware, and 2 bathrooms with a shower. Towels and bed linen are offered in the holiday home. For added privacy, the accommodation features a private entrance.

Location is so central to the city centre while still being quiet and having car parking close to hand.

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9.9
Exceptional
9 reviews
Price from
€ 323
per night

Featuring garden views, Walsingham House - Peaceful Elevated - Near Oram's Arbour provides accommodation with a garden and a terrace, around 21 km from The Mayflower Theatre. Both free WiFi and parking on-site are available at the holiday home free of charge. The property is non-smoking and is located 21 km from Southampton Guildhall.

Spotless. Incredibly well appointed. Amazing spot. Fantastic hosts.

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9.4
Superb
29 reviews
Price from
€ 320
per night

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.
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Most booked holiday homes in Winchester this month

Enjoy breakfast in Winchester!

  • Family home in Hampshire - Sleeps up to 9 people with 3 parking spaces
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 13 reviews

    Family home in Hampshire - Sleeps up to 9 people with 3 parking spaces, a property with a garden, is situated in Winchester, 21 km from Southampton Guildhall, 22 km from Southampton Cruise Terminal,...

    It had the space we needed and was very well presented.

  • Millstream House
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 45 reviews

    Boasting river views, Millstream House features accommodation with a garden and a patio, around 21 km from The Mayflower Theatre.

    The property was beautiful in a beautiful location.

  • 4 Bed City House with Private Garden and Parking
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 28 reviews

    Situated in Winchester and only 19 km from The Mayflower Theatre, 4 Bed City House with Private Garden and Parking features accommodation with garden views, free WiFi and free private parking.

    Great location. Close to the high street. Lovely property.

  • House situated on River Itchen
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 26 reviews

    Offering a garden and city view, House situated on River Itchen is located in Winchester, 22 km from Southampton Cruise Terminal and 25 km from Ageas Bowl.

    Fantastic property, very modern and fab location over looking the river.

  • Beautiful house on the River Itchen
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 27 reviews

    Situated in Winchester, 21 km from The Mayflower Theatre and 21 km from Southampton Guildhall, Beautiful house on the River Itchen features accommodation with free WiFi in a historic building.

    Lovely clean house with everything you need. Excellent location.

  • Sky View
    Breakfast options
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 37 reviews

    Set 21 km from Southampton Guildhall, 23 km from Southampton Cruise Terminal and 26 km from Ageas Bowl, Sky View provides accommodation located in Winchester.

    Amazing spacious place! Very clean and easy check in.

  • No2 St Peters Street
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 8 reviews

    Providing a garden, a bar and free WiFi, No2 St Peters Street is a recently renovated holiday home 20 km from The Mayflower Theatre and 20 km from Southampton Guildhall.

    The decor was beautiful and done to a really high standard. Everything was spotless and the location was perfect!

  • The Nestle House
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 12 reviews

    Located in Winchester, The Nestle House is a historic holiday home that provides free WiFi, and guests can enjoy a garden and a terrace. With city views, this accommodation offers a patio.

    The attention to detail was exceptional from the host.

Save money on holiday homes in Winchester – budget options available!

  • Mallard Cottage
    Budget options available
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 9 reviews

    Set in Winchester in the Hampshire region, Mallard Cottage offers accommodation with free WiFi and free private parking.

    The location was great, and off road parking was invaluable. The owners were very welcoming.

  • Walsingham House - Peaceful Elevated - Near Oram's Arbour
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 29 reviews

    Featuring garden views, Walsingham House - Peaceful Elevated - Near Oram's Arbour provides accommodation with a garden and a terrace, around 21 km from The Mayflower Theatre.

    It’s a wow property. Super clean. With all facilities

  • Hang Your Hat
    Budget options available
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 99 reviews

    Set in a former Brewery workers cottage built by Lord Northbrook in 1843, Hang Your Hat is situated in Winchester and offers accommodation with a private courtyard garden, free WiFi and a log...

    Home from home .Christmas tree was a lovely touch Would definitely recommend

  • South House
    Budget options available
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 86 reviews

    South House is located in Winchester, on the border of the scenic South Downs National Park. Free WiFi access is available in this holiday home.

    location was perfect for central town and cathedral

  • Hyde Brewery House - 2 bedroom house with parking
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 8 reviews

    Set 22 km from Southampton Guildhall, 23 km from Southampton Cruise Terminal and 27 km from Jane Austen's House Museum, Hyde Brewery House - 2 bedroom house with parking features accommodation located...

    Great property but v admin happy. Huge deposit required. Didn’t see or speak to anyone. No toilet roll or salt n pepper

  • Riverside 3 Bed House
    Budget options available
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 13 reviews

    Featuring river views, Riverside 3 Bed House provides accommodation with a garden and a patio, around 21 km from Southampton Guildhall.

    House was spotless. High street was just around the corner.

  • Queens Road Rental - Winchester Accommodation
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 7 reviews

    Set in Winchester, 21 km from The Mayflower Theatre and 21 km from Southampton Guildhall, Queens Road Rental - Winchester Accommodation offers accommodation with free WiFi, a garden, and access to a...

    The location was excellent. The property was clean and tidy and a small provisions pack made available.

  • Beggar's Lane Cottage
    Budget options available
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 66 reviews

    Housed in a historic building, Beggar's Lane Cottage features accommodation with a garden and free WiFi in Winchester, 21 km from The Mayflower Theatre.

    Easy to find, walking distance to town, very sweet property

Great access to the city centre! Check these holiday homes in Winchester

  • Piping Green 5 bedroom House
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Piping Green 5 bedroom House, a property with a garden, is set in Winchester, 15 km from The Mayflower Theatre, 16 km from Southampton Guildhall, as well as 17 km from Southampton Cruise Terminal.

  • Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 16
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 4 reviews

    Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 16 is set in Winchester, 12 km from Ageas Bowl, 17 km from The Mayflower Theatre, and 17 km from Southampton Guildhall.

  • The Old Brewery Boardroom - Winchester City Centre, Free Parking for 2 Cars, Sleeps 6
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 3 reviews

    Housed in a historic building, the recently renovated The Old Brewery Boardroom - Winchester City Centre, Free Parking for 2 Cars, Sleeps 6 offers accommodation with a garden and free WiFi.

  • The Manor House at Norton Park
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Located in Winchester, in a historic building, 20 km from Highclere Castle, The Manor House at Norton Park is a recently renovated holiday home with a garden and barbecue facilities.

  • Charming 4-Bed House in Winchester Free Parking
    7.3
    Scored 7.3
    Good
    Rated good
     · 3 reviews

    Offering a garden and garden view, Charming 4-Bed House in Winchester Free Parking is located in Winchester, 21 km from Southampton Guildhall and 23 km from Southampton Cruise Terminal.

  • The Old Sweet Shop
    7.0
    Scored 7.0
    Good
    Rated good
     · 1 review

    The Old Sweet Shop, a property with a garden, is situated in Winchester, 18 km from Southampton Guildhall, 20 km from Southampton Cruise Terminal, as well as 23 km from Ageas Bowl.

  • No 5 Winchester

    No 5 Winchester, a property with a garden, is set in Winchester, 20 km from Southampton Guildhall, 21 km from Southampton Cruise Terminal, as well as 24 km from Ageas Bowl.

  • 3BR Chic House, central Winchester- Sleeps 7!

    Situated in Winchester, 20 km from The Mayflower Theatre and 20 km from Southampton Guildhall, 3BR Chic House, central Winchester- Sleeps 7!

  • Stylish 2-BR Central Location, Sleeps 6, Winchester

    Offering a garden and garden view, Stylish 2-BR Central Location, Sleeps 6, Winchester is set in Winchester, 20 km from Southampton Guildhall and 22 km from Southampton Cruise Terminal.

  • 2-BR Cosy Retreat, with Garden, central Winchester by Blue Puffin Stays

    Offering a garden and garden view, 2-BR Cosy Retreat, with Garden, central Winchester by Blue Puffin Stays is set in Winchester, 21 km from Southampton Guildhall and 22 km from Southampton Cruise...

  • 59 Bar End Road

    Set 20 km from The Mayflower Theatre, 59 Bar End Road offers accommodation with free WiFi and free private parking.

  • Little Hampden
    Central location

    Offering quiet street views, Little Hampden is an accommodation set in Winchester, 14 km from Southampton Guildhall and 15 km from Southampton Cruise Terminal.

  • 4 Bed in Redlynch 82799

    Set in Winchester and only 19 km from Salisbury Cathedral, 4 Bed in Redlynch 82799 offers accommodation with garden views, free WiFi and free private parking.

FAQ about holiday homes in Winchester






Holiday homes that guests love in Winchester

  • Avg. price/night: € 129.01
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 59 reviews
    Very clean and comfortable - the smell of the room made me feel like I was in a spa! Loved the extra touches (tea and coffee facilities) and soaps. Very accommodating to letting me have a later check out time so I could sleep after my night shift! I would 100% love to stay again (when not working!) Was lovely to sit on the terrace to eat dinner in the sun.
    Olivia
    Solo traveller
  • Avg. price/night: € 199.49
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 1,454 reviews
    We were glad of the Wykeham Arms car park as the roads are very old and narrow and we couldn’t see other parking. The accommodation we stayed in opposite the pub (still part of the Wykeham Arms) was old and quirky and the sun was streaming into the bedroom when we arrived late afternoon. Very clean and comfortable and stylishly decorated but still in keeping with the age. The breakfast was delicious!
    Fiona
    Young couple
  • 9.3
    Scored 9.3
    Superb
    Rated superb
     · 240 reviews
    Lovely spot Very clean and felt luxurious
    Louisa
    Family with young children
  • 8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 250 reviews
    Great location and very clean
    Aimee
    Young couple
  • Avg. price/night: € 186.48
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 417 reviews
    Very clean and comfortable. The luxury bath was a great feature.
    Lisa
    Young couple
  • 9.0
    Scored 9.0
    Superb
    Rated superb
     · 41 reviews
    The location is great with walking distance to Winchester city centre. The whole house is very clean and parking is nearby. The kitchen and bedrooms are really good. Overall a very good place to stay in Winchester for a small group of people .
    HU
    People with friends
  • Avg. price/night: € 141.91
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 931 reviews
    Very clean and friendly pub and great value 👌
    markdonhou
    Family with young children
  • Avg. price/night: € 129.01
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 59 reviews
    Very clean, quiet.
    Sharon
    Young couple
  • 9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 9 reviews
    I have stay in a lot of holiday homes and one was by far the best. High spec and accommodating hosts.
    Brian
    People with friends
  • 9.0
    Scored 9.0
    Superb
    Rated superb
     · 4 reviews
    Everything was wonderful. Feels like home, it was very clean and comfortable. Additionally the landlady was too sweet and caring. This holiday home is surely one of the best place to stay in Winchester. Will miss this place alot as it was such a beautiful place to stay. Thank you Miss.Lund for everything during our stay :)
    Evanglin
    Solo traveller

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